Ambroxol

Details

• Internal ID: 66e3c3ca-2543-4622-a9af-a4a0438934e4
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylmethylamines
• IUPAC Name: 4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol
• SMILES (Canonical): C1CC(CCC1NCC2=C(C(=CC(=C2)Br)Br)N)O
• SMILES (Isomeric): C1CC(CCC1NCC2=C(C(=CC(=C2)Br)Br)N)O
• InChI: InChI=1S/C13H18Br2N2O/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10/h5-6,10-11,17-18H,1-4,7,16H2
• InChI Key: JBDGDEWWOUBZPM-UHFFFAOYSA-N
• Popularity: 1,772 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₈Br₂N₂O
• Molecular Weight: 378.10 g/mol
• Exact Mass: 377.97654 g/mol
• Topological Polar Surface Area (TPSA): 58.30 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 18683-91-5
• 107814-37-9
• rac-cis-Ambroxol
• 36557-04-7
• Ambroxol Base
• 4-((2-amino-3,5-dibromobenzyl)amino)cyclohexan-1-ol
• Ambroxolum
• Bisolvon metabolite VIII
• Bromhexine-metabolite VIII
• NA-872
• Tabcin
• trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol
• Ambroxol, cis-
• cis-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol
• Ambroxol [INN]
• Cyclohexanol, 4-[[(2-amino-3,5-dibromophenyl)methyl]amino]-, trans-
• 4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol
• trans-4-((2-Amino-3,5-dibromobencil)amino)ciclohexanol
• trans-4-((2-Amino-3,5-dibromobenzyl)amine)cyclohexanol
• QH6ZT6J071
• Cyclohexanol, 4-((2-amino-3,5-dibromobenzyl)amino)- (E)-
• N-(2-Amino-3,4-dibromocyclohexyl)-trans-4-aminocyclohexanol
• 4-Hydroxydemethylbromhexine, cis-
• N-(trans-4-Hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)-amine
• N-(trans-p-Hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)amine
• Ambroxol (INN)
• Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, trans-
• 200168S0CL
• trans-4-[(2-amino-3,5-dibromobenzyl)amino]cyclohexanol
• N-(2-Amino-3,4-dibromociclohexil)-trans-4-aminociclohexanol
• N-(trans-4-Hidroxiciclohexil)-(2-amino-3,5-dibromobencil)amina
• 1217679-83-8
• Ambroxol [INN:BAN]
• cis-4-(((2-Amino-3,5-dibromophenyl)methyl)amino)cyclohexanol
• Ambroxolum [INN-Latin]
• Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, cis-
• Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, trans- (9CI)
• Bromhexine Metabolite VIII
• NCGC00016781-04
• EINECS 242-500-3
• CAS-23828-92-4
• Amboxol
• cis-Ambroxol
• SR-05000001463
• UNII-200168S0CL
• Tabcin (TN)
• Spectrum_001346
• AMBROXOL [MI]
• Prestwick0_000366
• Prestwick1_000366
• Prestwick2_000366
• Prestwick3_000366
• Spectrum2_001518
• Spectrum3_000955
• Spectrum4_001068
• Spectrum5_001021
• trans-4-((2-Amino-3,5-dibromobencil)amino)ciclohexanol [Spanish]
• N-(2-Amino-3,4-dibromociclohexil)-trans-4-aminociclohexanol [Spanish]
• AMBROXOL [WHO-DD]
• EC 242-500-3
• N-(trans-4-Hidroxiciclohexil)-(2-amino-3,5-dibromobencil)amina [Spanish]
• UNII-QH6ZT6J071
• Oprea1_766685
• SCHEMBL18702
• BSPBio_000491
• KBioGR_001396
• KBioSS_001826
• MLS001306470
• DivK1c_000027
• SCHEMBL423712
• SPBio_001595
• SPBio_002412
• BPBio1_000541
• CHEMBL153479
• SCHEMBL7855003
• 4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol
• CHEMBL1477775
• DTXSID8022583
• SCHEMBL21765132
• BCBcMAP01_000092
• CHEBI:92994
• GTPL10692
• KBio1_000027
• KBio2_001826
• KBio2_004394
• KBio2_006962
• KBio3_002050
• DTXSID60860228
• CHEBI:135590
• JBDGDEWWOUBZPM-XYPYZODXSA-N
• NINDS_000027
• 4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol
• HMS2089D06
• HMS2231B19
• HMS3373J22
• HMS3886M18
• BCP04489
• HY-B1039
• BDBM50395322
• MFCD00242702
• MFCD28143339
• s5710
• AKOS005530704
• AKOS015889660
• AKOS027338704
• AC-8362
• Ambroxol hydrochloride impurity D [EP]
• BCP9000283
• CCG-207907
• CS-4558
• DB06742
• SB17463
• SB82866
• IDI1_000027
• SMP1_000014
• NCGC00016781-01
• NCGC00016781-02
• NCGC00016781-08
• NCGC00159399-02
• NCGC00371077-02
• AS-56023
• SMR000718792
• VS-02240
• 4-HYDROXYDEMETHYLBROMHEXINE, TRANS-
• BCP0726000066
• SBI-0051766.P002
• AB00514663
• CS-0323348
• FT-0622261
• FT-0630430
• FT-0661549
• D07442
• AB00053639_13
• AB01275465-01
• A813089
• EN300-18524079
• Q221637
• SR-05000001463-1
• AMBROXOL HYDROCHLORIDE IMPURITY D [EP IMPURITY]
• BRD-K11223672-003-03-7
• BRD-K11223672-003-04-5
• BRD-K56558538-003-02-8
• 4-[(2-amino-3,5-dibromophenyl)methylamino-]cyclohexanol
• 4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexanol
• (1s,4s)-4-((2-amino-3,5-dibromobenzyl)amino)cyclohexanol
• 4-[(2-Amino-3,5-dibromobenzyl)amino]cyclohexanol, trans-
• (1r,4r)-4-((2-amino-3,5-dibromobenzyl)amino)cyclohexan-1-ol
• trans-4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexanol
• (1r,4r)-4-{[(2-Amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol
• Cyclohexanol, 4-[[(2-amino-3,5-dibromo-phenyl)methyl]amino]-, trans

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9296	92.96%
Caco-2	+	0.5995	59.95%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.9000	90.00%
Subcellular localzation	Mitochondria	0.3973	39.73%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.9552	95.52%
OATP1B3 inhibitior	+	0.9456	94.56%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6649	66.49%
P-glycoprotein inhibitior	-	0.9469	94.69%
P-glycoprotein substrate	-	0.6311	63.11%
CYP3A4 substrate	+	0.5114	51.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5483	54.83%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8933	89.33%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.7471	74.71%
CYP inhibitory promiscuity	+	0.6653	66.53%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7862	78.62%
Carcinogenicity (trinary)	Non-required	0.6084	60.84%
Eye corrosion	-	0.9347	93.47%
Eye irritation	-	0.8959	89.59%
Skin irritation	-	0.6861	68.61%
Skin corrosion	-	0.8665	86.65%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3945	39.45%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7446	74.46%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.9042	90.42%
Acute Oral Toxicity (c)	IV	0.6174	61.74%
Estrogen receptor binding	+	0.8009	80.09%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.6245	62.45%
Glucocorticoid receptor binding	-	0.5659	56.59%
Aromatase binding	+	0.5721	57.21%
PPAR gamma	+	0.7350	73.50%
Honey bee toxicity	-	0.9037	90.37%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.7908	79.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.82%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.34%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	95.47%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.92%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.21%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.93%	89.62%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	89.15%	97.23%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.24%	95.58%
CHEMBL308	P06493	Cyclin-dependent kinase 1	85.07%	91.73%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.90%	92.94%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	82.70%	80.33%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.19%	90.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.84%	95.89%
CHEMBL4208	P20618	Proteasome component C5	81.34%	90.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.22%	92.88%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	80.27%	94.01%

Plants that contains it

• Justicia adhatoda

Cross-Links

• PubChem: 2132
• LOTUS: LTS0192847
• wikiData: Q105124245